TY - JOUR
T1 - Rearrangement during halogenation of 2-hydroxy-1,2-diphenylpropan-1-one (α-methylbenzoin)
AU - Aitken, Kati Marianne
AU - Aitken, Robert Alan
PY - 2008/5/26
Y1 - 2008/5/26
N2 - The reaction of 2-hydroxy-1,2-diphenylpropan-1-one 1 with SOCl2 or PBr3 gives, respectively, the 3-chloro- and 3-bromo-1,2-diphenylpropan-1-ones 4 and 6. The expected 2-chloro- and 2-bromo-1,2-diphenylpropan-1-ones 2 and 5 can, however, be formed by treatment of 1,2-diphenylpropan-1-one 8 with Cl-2 or Br-2/AlCl3. The four halogenated products are characterised by H-1 and C-13 NMR spectroscopy for the first time. (c) 2008 Elsevier Ltd. All rights reserved.
AB - The reaction of 2-hydroxy-1,2-diphenylpropan-1-one 1 with SOCl2 or PBr3 gives, respectively, the 3-chloro- and 3-bromo-1,2-diphenylpropan-1-ones 4 and 6. The expected 2-chloro- and 2-bromo-1,2-diphenylpropan-1-ones 2 and 5 can, however, be formed by treatment of 1,2-diphenylpropan-1-one 8 with Cl-2 or Br-2/AlCl3. The four halogenated products are characterised by H-1 and C-13 NMR spectroscopy for the first time. (c) 2008 Elsevier Ltd. All rights reserved.
KW - KETONES
UR - http://www.scopus.com/inward/record.url?scp=42749092163&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2008.03.043
DO - 10.1016/j.tet.2008.03.043
M3 - Article
SN - 0040-4020
VL - 64
SP - 5217
EP - 5220
JO - Tetrahedron
JF - Tetrahedron
ER -